(1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde

Base Information

• Chemical Name: (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde
• CAS No.: 304859-86-7
• Molecular Formula: C₁₅H₁₉BrO₃
• Molecular Weight: 327.218
• Mol file: 304859-86-7.mol

Synonyms:(1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde

Chemical Property of (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde

There total 1 articles about (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

(1'S)-3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzaldehyde (185967-11-7) → (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde (304859-86-7)

Guidance literature:

With bromine; In dichloromethane;

DOI:10.1021/ja001455r

Reference yield: 75.0%

dimethyl sulfate (77-78-1) + (1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde (304859-86-7) → (1'S)-2-Bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde (304859-87-8)

Guidance literature:

With potassium carbonate; In acetone;

DOI:10.1021/ja001455r

Reference yield:

(1'S)-2-bromo-3,4-dihydroxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde (304859-86-7) → (M,1''S,1'''S)-2-hydroxy-6'-hydroxymethyl-3,2',3'-trimethoxy-6-methyl-4,4'-di-(1,2,2-trimethylcyclopentyl)biphenyl

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / K₂CO₃ / acetone

2.1: 97 percent / NaClO₂; amidosulfonic acid; NaOAc / dioxane; acetic acid; H₂O / 0 - 20 °C

3.1: SOCl₂ / 20 °C

4.1: NaH / tetrahydrofuran / 0.5 h

4.2: 87 percent / CH₂Cl₂; tetrahydrofuran

5.1: 39 percent / PPh₃; NaOAc / (Ph₃P)2PdCl₂ / N,N-dimethyl-acetamide / 15 h / 110 °C

6.1: LiAlH₄ / tetrahydrofuran / 20 °C

With sodium chlorite; lithium aluminium tetrahydride; thionyl chloride; aminosulfonic acid; sodium acetate; sodium hydride; potassium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl acetamide; water; acetic acid; acetone;

DOI:10.1021/ja001455r

upstream raw materials:

(1'S)-3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzaldehyde

Downstream raw materials:

(1'S)-2-Bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde

(1'S)-2-bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzoic acid

(1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate